Phenoxyethanol
Names | |
---|---|
IUPAC name
2-Phenoxyethanol | |
Other names
Phenoxyethanol Ethylene glycol monophenyl ether Phenoxytolarosol Dowanol EP / EPH Emery 6705 Rose ether 1-Hydroxy-2-phenoxyethane β-hydroxyethyl phenyl ether Phenyl cellosolve | |
Identifiers | |
122-99-6 | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:64275 |
ChEMBL | ChEMBL1229846 |
ChemSpider | 13848467 |
ECHA InfoCard | 100.004.173 |
PubChem | 31236 |
UNII | HIE492ZZ3T |
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Properties | |
C8H10O2 | |
Molar mass | 138.17 g·mol−1 |
Appearance | Colorless oily liquid |
Odor | faint rose-like |
Density | 1.102 g/cm3 |
Melting point | −2 °C (28 °F; 271 K) |
Boiling point | 247 °C (477 °F; 520 K) |
26 g/kg | |
Solubility | Chloroform, Alkali, diethyl ether: soluble |
Solubility in arachis oil | slightly |
Solubility in olive oil | slightly |
Solubility in acetone | miscible |
Solubility in ethanol | miscible |
Solubility in glycerol | miscible |
Vapor pressure | 0.001 kPa |
Thermal conductivity | 0.169 W/(m⋅K) |
Refractive index (nD) |
1.534 (20 ℃) |
Hazards | |
NFPA 704 | |
Flash point | 121 °C (250 °F; 394 K) |
Related compounds | |
Related compounds |
phenetole |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references | |
Phenoxyethanol is a germicidal and germistatic glycol ether, phenol ether, and aromatic alcohol often used together with quaternary ammonium compounds.
Use
Phenoxyethanol is used as a perfume fixative; an insect repellent; an antiseptic; a solvent for cellulose acetate, dyes, inks, and resins; a preservative for pharmaceuticals, cosmetics and lubricants; an anesthetic in fish aquaculture; and in organic synthesis.
Phenoxyethanol is an alternative to formaldehyde-releasing preservatives.[4] In Japan and the EU, its concentration in cosmetics is restricted to 1%.[5]
Production
Phenoxyethanol is produced by the hydroxyethylation of phenol (Williamson synthesis), for example, in the presence of alkali-metal hydroxides or alkali-metal borohydrides.[1]
Efficacy
Phenoxyethanol is effective against gram-negative and gram-positive bacteria, and the yeast Candida albicans.[6]
Aromatic alcohol | Concentration, % | Contact time, min | |||
---|---|---|---|---|---|
Escherichia coli | Pseudomonas aeruginosa | Proteus mirabilis | Staphylococcus aureus | ||
Benzyl alcohol | 1 | >30 | >30 | >30 | >30 |
Phenethyl alcohol | 1.25 | 2.5 | 2.5 | 2.5 | >30 |
2.5 | 2.5 | 2.5 | 2.5 | 5 | |
Phenoxyethanol | 1.25 | 15 | 2.5 | 2.5 | >30 |
2.5 | 2.5 | 2.5 | 2.5 | >30 |
Safety
Phenoxyethanol is a vaccine preservative and potential allergen, which may result in a nodular reaction at the site of injection.[8] It is neurotoxic.[9] Ingestion may cause CNS and respiratory depression, vomiting and diarrhea in infants, particularly when combined with chlorphenesin.[10]
References
- 1 2 Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe; Wilfried Paulus (2007), "Phenol Derivatives", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, doi:10.1002/14356007.a19_313
- ↑ "Phenoxyethanol", British Pharmacopoeia, 2, 2009, ISBN 978-0-11-322799-0
- ↑ David R. Lide, ed. (2010), CRC Handbook of Chemistry and Physics (90th ed.), CRC Press
- ↑ Wineski LE, English AW (1989). "Phenoxyethanol as a nontoxic preservative in the dissection laboratory". Acta Anat (Basel). 136 (2): 155–8. doi:10.1159/000146816. PMID 2816264.
- ↑ Tokunaga H, Takeuchi O, Ko R, Uchino T, Ando M (2003). "市販化粧水中のフェノキシエタノールおよびパラベン類の分析法に関する研究" [Studies for analyzing phenoxyethanol and parabens in commercial lotions] (PDF). Kokuritsu Iyakuhin Shokuhin Eisei Kenkyūjo Hōkoku (in Japanese) (121): 25–9. PMID 14740401.
- ↑ Lowe I, Southern J (1994). "The antimicrobial activity of phenoxyethanol in vaccines". Lett Appl Microbiol. 18 (2): 115–6. doi:10.1111/j.1472-765X.1994.tb00820.x. PMID 7764595.
- ↑ Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551
- ↑ M. H. Beck; S. M. Wilkinson (2010), "Contact Dermatitis: Allergic", in Tony Burns; Stephen Breathnach; Neil Cox; Christopher Griffiths, Rook's Textbook of Dermatology, 2 (8th ed.), Wiley-Blackwell, p. 26.46, ISBN 978-1-4051-6169-5
- ↑ Schmuck G, Steffens W, Bomhard E (July 2000). "2-Phenoxyethanol: a neurotoxicant?". Archives of Toxicology. 74 (4-5): 281–7. doi:10.1007/s002040000110. PMID 10959804.
- ↑ "FDA Warns Consumers Against Using Mommy's Bliss Nipple Cream".